Lipase-catalyzed syntheses of sugar esters in non-aqueous media

Biotechnology Letters

Volumn 33, Issue 10, 2011, Pages 1911-1919

  Kobayashi, Takashi ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Lipase; Non aqueous medium; Productivity; Sugar derivative; Sugar ester

Indexed keywords

LIPASE-CATALYZED; LIPASE-CATALYZED SYNTHESIS; NON-AQUEOUS MEDIUM; NONAQUEOUS MEDIA; SUGAR DERIVATIVE; SUGAR DERIVATIVES; SUGAR ESTER; SUGAR ESTERS; SYNTHETIC METHODS;

CATALYSIS; ESTERIFICATION; ESTERS; IONIC LIQUIDS; LIPASES; ORGANIC SOLVENTS; PRODUCTIVITY; SUGARS; SYNTHESIS (CHEMICAL);

LIQUID SUGAR;

CARBOHYDRATE; ESTER; TRIACYLGLYCEROL LIPASE;

BIOCATALYSIS; BIOSYNTHESIS; BIOTECHNOLOGY; CHEMISTRY; ESTERIFICATION; METABOLISM; METHODOLOGY; REVIEW; SYNTHESIS;

BIOCATALYSIS; BIOTECHNOLOGY; CARBOHYDRATES; ESTERIFICATION; ESTERS; LIPASE;

EID: 80052811116     PISSN: 01415492     EISSN: 15736776     Source Type: Journal    
DOI: 10.1007/s10529-011-0663-z     Document Type: Review

References (51)

1. Arcos JA, Bernabé M, Otero C (1998) Quantitative enzymatic production of 6-O-acylglucose esters. Biotechnol Bioeng 57: 505-509.
2. Ardhaoui M, Falcimaigne A, Ognier S, Engasser JM, Moussou P, Pauly G, Ghoul M (2004) Effect of acyl donor chain length and substitutions pattern on the enzymatic acylation of flavonoids. J Biotechnol 110: 265-271.
3. Castillo E, Pezzotti F, Navarro A, López-Munguía A (2003) Lipase-catalyzed synthesis of xylitol monoesters: solvent engineering approach. J Biotechnol 1024: 251-259.
4. Cauglia F, Canepa P (2008) The enzymatic synthesis of glucosylmyristate as a reaction model for general considerations on 'sugar esters' production. Biores Technol 99: 4065-4072.
5. Chen J, Kimura Y, Adachi S (2005) Continuous synthesis of 6-O-linoleoyl hexose using a packed-bed reactor system with immobilized lipase. Biochem Eng J 22: 145-149.
6. Chen J, Kimura Y, Adachi S (2007) Surface activities of monoacyl trehaloses in aqueous solution. LWT 40: 412-417.
7. Chopineau J, McCafferty FD, Therisod M, Klibanov AM (1988) Production of biosurfactants from sugar alcohols and vegetable oils catalyzed by lipases in a nonaqueous medium. Biotechnol Bioeng 31: 208-214.
8. Coulon D, Ismail A, Girardin M, Ghoul M (1998) Enzymatic synthesis of alkylglycoside fatty acid esters catalyzed by an immobilized lipase. J Mol Catal B Enzym 5: 45-48.
9. Cramer JF, Dueholm MS, Nielsen SB, Pedersen DS, Wimmer R, Pedersen LH (2007) Controlling the degree of esterification in lipase catalysed synthesis of xylitol fatty acid esters. Enzym Microb Technol 41: 346-352.
10. Diego TD, Lozano P, Gmouh S, Vaultier M, Iborra JL (2005) Understanding structure-stability relationships of Candida antartica lipase B in ionic liquids. Biomacromol 6: 1457-1464.
11. Ferrer M, Cruces MA, Bernabé M, Ballesteros A, Plou FJ (1999) Lipase-catalyzed regioselective acylation of sucrose in two-solvent mixtures. Biotechnol Bioeng 65: 10-16.
12. Ferrer M, Cruces MA, Plou FJ, Bernabé M, Ballesteros A (2000) A simple procedure for the regioselective synthesis of fatty acid esters of maltose, leucrose, maltotriose and n-dodecyl maltosides. Tetrahedron 56: 4053-4061.
13. Ferrer M, Soliveri J, Plou FJ, López-Cortés N, Reyes-Duarte D, Christensen M, Copa-Patiño JL, Ballesteros A (2005) Synthesis of sugar esters in solvent mixtures by lipases from Thermomyces lanuginosus and Candida antarctica B, and their antimicrobial properties. Enzym Microb Technol 36: 391-398.
14. Fregapane G, Sarney DB, Vulfson EN (1991) Enzymic solvent-free synthesis of sugar acetal fatty acid esters. Enzym Microb Technol 13: 796-800.
15. Gao C, Whitcombe MJ, Vulfson EN (1999) Enzymatic synthesis of dimeric and trimeric sugar-fatty acid esters. Enzym Microb Technol 25: 264-270.
16. Ikeda I, Klibanov AM (1993) Lipase-catalyzed acylation of sugars solubilized in hydrophobic solvents by complexation. Biotechnol Bioeng 42: 788-791.
17. Kaar JL, Jesionowski AM, Berberich JA, Moulton R, Russell AJ (2003) Impact of ionic liquid physical properties on lipase activity and stability. J Am Chem Soc 125: 4125-4131.
18. Katsoura MH, Polydera AC, Katapodis P, Kolisis FN, Stamatis H (2007) Effect of different reaction parameters on the lipase-catalyzed selective acylation of polyhydroxylated natural compounds in ionic liquids. Proc Biochem 42: 1326-1334.
19. Khaled N, Montet D, Pina M, Graille J (1991) Fructose oleate synthesis in a fixed catalyst bed reactor. Biotechnol Lett 13: 167-172.
20. Kim MJ, Choi MY, Lee JK, Ahn Y (2003) Enzymatic selective acylation of glycosides in ionic liquids: significantly enhanced reactivity and regioselectivity. J Mol Catal B Enzym 26: 115-118.
21. Klibanov AM (1986) Enzymes that work in organic solvents. ChemTech 16: 354-359.
22. Klibanov AM (1989) Enzymatic catalysis in anhydrous organic solvents. TIBS 14: 141-144.
23. Klyosov AA, van Viet N, Berezin IV (1975) The reactions of α-chymotrypsin and related proteins with ester substrates in non-aqueous solvents. Eur J Biochem 59: 3-7.
24. Kobayashi T, Adachi S, Matsuno R (2003a) Lipase-catalyzed condensation of p-methoxyphenethyl alcohol and carboxylic acids with different steric and electrical properties in acetonitrile. Biotechnol Lett 25: 3-7.
25. Kobayashi T, Furutani W, Adachi S, Matsuno R (2003b) Equilibrium constant for the lipase-catalyzed synthesis of fatty acid butyl ester in various organic solvents. J Mol Catal B Enzym 24: 61-66.
26. Kobayashi T, Ehara T, Mizuoka T, Adachi S (2010) Efficient synthesis of 6-O-palmitoyl-1, 2-O-isopropylidenea-D-glucofuranose in an organic solvent system by lipase-catalyzed esterification. Biotechnol Lett 32: 1679-1684.
27. Krishna SH, Divakar S, Prapulla SG, Karanth NG (2001) Enzymatic synthesis of isoamyl acetate using immobilized lipase from Rhizomucor miehei. J Biotechnol 87: 193-201.
28. Lee SH, Ha SH, Hiep NM, Chang W-J, Koo YM (2008) Lipase-catalyzed synthesis of glucose fatty acid ester using ionic liquids mixtures. J Biotechnol 133: 486-489.
29. Lozano P, Diego T, Gmouh S, Vaultier M, Iborra JL (2004) Criteria to design green enzymatic processes in ionic liquid/supercritical carbon dioxide systems. Biotechnol Progr 20: 661-669.
30. Lue BM, Guo Z, Glasius M, Xu X (2010) Scalable preparation of high purity rutin fatty acid esters. J Am Oil Chem Soc 87: 55-61.
31. Matsuo T, Kobayashi T, Kimura Y, Hosoda A, Taniguchi H, Adachi S (2008) Continuous synthesis of glyceryl ferulate using immobilized Candida antarctica lipase. J Oleo Sci 57: 375-380.
32. Moreau B, Lognay GC, Blecker C, Brohéel JC, Chéry F, Rollin P, Paquot M, Marlier M (2004) Synthesis of novel D-glucuronic acid fatty esters using Candida antarctica lipase in tert-butanol. Biotechnol Lett 26: 419-424.
33. Nakajima N, Ishihara K, Itoh T, Furuya T, Hamada H (1999) Lipase-catalyzed direct and regioselective acylation of flavonoid glucoside for mechanistic investigation of stable plant pigments. J Biosci Bioeng 87: 105-107.
34. Otto RT, Bornscheuer UT, Syldatk C, Schmid RD (1998) Synthesis of aromatic n-alkyl-glucoside esters in a coupled β-glucosidase and lipase reaction. Biotechnol Lett 20: 437-440.
35. Pinsirodom P, Watanabe Y, Nagao T, Sugihara A, Kobayashi T, Shimada Y (2004) Critical temperature for production of MAG by esterification of different FA with glycerol using Penicillium camembertii lipase. J Am Oil Chem Soc 81: 543-547.
36. Plou FJ, Cruces MA, Ferrer M, Fuentes G, Pastor E, Bernabé M, Christensen M, Comelles F, Parra JL, Ballesteros A (2002) Enzymatic acylation of di- and trisaccharides with fatty acids: choosing the appropriate enzyme, support and solvent. J Biotechnol 96: 55-66.
37. Sarney DB, Kapeller H, Fregapane G, Vulfson EN (1994) Chemo-enzymatic synthesis of disaccharide fatty acid esters. J Am Oil Chem Soc 71: 711-714.
38. Sarney DB, Barnard MJ, MacManus DA, Vulfson EN (1996) Application of lipases to the regiosolective synthesis of sucrose fatty acid monoesters. J Am Oil Chem Soc 73: 1481-1487.
39. Somashekar BR, Divakar S (2007) Lipase catalyzed synthesis of L-alanyl esters of carbohydrates. Enzym Microb Technol 40: 299-309.
40. Stamatis H, Sereti V, Kolisis FN (2001) Enzymatic synthesis of hydrophilic and hydrophobic derivatives of natural phenolic acids in organic media. J Mol Catal B Enzym 11: 323-328.
41. ®). Enzym Microb Technol 39: 1236-1241.
42. Therisod M, Klibanov AM (1986) Facile enzymatic preparation of monoacylated sugars in pyridine. J Am Chem Soc 108: 5638-5640.
43. Vijayakumar GR, Lohith K, Somashekar BR, Divakar S (2004) Lipase catalyzed synthesis of L-alanyl, L-leucyl and L-phenylalanyl esters of d-glucose using unprotected amino acids. Biotechnol Lett 26: 1323-1328.
44. Watanabe Y, Miyawaki Y, Adachi S, Nakanishi K, Matsuno R (2000) Synthesis of lauroyl saccharides through lipase-catalyzed condensation in microaqueous water-miscible solvents. J Mol Catal B Enzym 10: 241-247.
45. Watanabe Y, Miyawaki Y, Adachi S, Nakanishi K, Matsuno R (2001) Equilibrium constant for lipase-catalyzed condensation of mannose and lauric acid in water-miscible organic solvents. Enzym Microb Technol 29: 494-498.
46. Watanabe Y, Shimada Y, Yamauchi-Sato Y, Kasai M, Yamamoto T, Tsutsumi K, Tominaga Y, Sugihara A (2002) Synthesis of MAG of CLA with Penicillium camembertii lipase. J Am Oil Chem Soc 79: 891-896.
47. Watanabe Y, Yamauchi-Sato Y, Nagao T, Negishi S, Terai T, Kobayashi T, Shimada Y (2005) Production of MAG of CLA by esterification with dehydration at ordinary temperature using Penicillium camembertii lipase. J Am Oil Chem Soc 82: 619-623.
48. Yamauchi-Sato Y, Watanabe Y, Nagao T, Negishi S, Kobayashi T, Shimada Y (2005) Production of diglycerol conjugated linoleic acid monoester by esterification with Penicillium camembertii lipase. J Oleo Sci 9: 481-486.
49. Yang RL, Li N, Li RF, Smith TJ, Zong MH (2010) A highly regioselective route to arbutin esters by immobilized lipase from Penicillium expansum. Biores Technol 101: 1-5.
50. Yu HL, Xu JH, Su JH, Lu WY, Lin GQ (2008) Synthesis of novel salidroside esters by lipase-mediated acylation with various functional acyl groups. J Biosci Bioeng 106: 65-68.
51. Zhao H, Baker GA, Song Z, Olubajo O, Crittlea T, Peters D (2008) Designing enzyme-compatible ionic liquids that can dissolve carbohydrates. Green Chem 10: 696-705.